Love is in the air, and there's no better place to cherish it than on Long Island, where romance finds its perfect backdrop amidst the serene beaches, charming towns, centuries-old historic sites, and enchanting landscapes. Whether you're looking for your next perfect date spot, an unrivalled setting to pop the question, or a dreamy honeymoon escape, Long Island offers the perfect trip for every romantic occasion, in every season. 

Read on lovebirds, as we unveil the ultimate guide to celebrating love on Long Island.


Swoonworthy Settings for Capturing Romantic Moments

Montauk Lighthouse.jpg

Long Island’s coastlines are a mosaic of beachfronts and historic waterfront villages that offer enough charm to be the set of a romantic comedy or Hallmark Christmas movie.  While Long Islanders may be biased towards their own Main Street scene, a hidden gem nestled on the North Shore worth exploring for date night is Sea Cliff. At only one square mile, Sea Cliff boasts its own beach and 16 neighborhood parks.  Sitting atop a 120-foot bluff, with meandering streets overlooking Hempstead Harbor and Long Island Sound, the waterfront community offers dramatic views of bobbing boats and traditional Victorian houses and antique shops, nestled throughout the cliffside.

On the other end of the Island, you’ll find the off-beat Hamptons Village of Sag Harbor. Originally a whaling port, this historic, Instagrammable downtown is filled with small restaurants, boutiques, and antique shops – many of which are located in restored whaling cottages from the 19th century, often adorned in dandling ivy and other greenery. Watch the rich and famous dock their yachts or grab a photo of the iconic Sag Harbor Cinema, built in 1890 to host vaudeville and burlesque shows.

Experience romance in the Hamptons this Valentine’s Day (minus the crowds!). Stroll the boutique-lined Main Streets of East Hampton or dine at chic restaurants that you’ll actually be able to get into.

Insider tip: Looking for the perfect romantic setting to pop the question? Consider these spots!


Feel Like Royalty with a Gilded Age Romance


Enjoy the beauty and serenity of Long Island’s Gold Coast region where New York’s elite built their mansions, castles, estates, and gardens high upon the North Shore bluffs during the 1920s “Gold Coast” era. Immortalized in F. Scott Fitzgerald’s “The Great Gatsby”, these former homes are known for their sophistication and opulence. Feel like royalty this Valentine’s Day and beyond, by perusing the great rooms that once played host to foreign diplomats, Hollywood royalty, and socialites.

Stay overnight at the breathtakingly beautiful historic mansion Oheka Castle. Walk the grounds and take a step back in time to a period of splendor with a mansion tour at Sands Point Preserve, the elegant estate at Old Westbury Gardens, or the historic estate of Coe Hall at Planting Fields.


Wine and Dine on the East End


Experience a picturesque weekend getaway with your loved one when you visit Long Island’s East End - either making your way through the island’s award-winning wine region, also known as the North Fork, or living your best luxurious life throughout the Hamptons on Long Island’s South Fork.

Cozy up inside an elaborate winter igloo and enjoy bungalow-style dining with a view at various vineyards on the North Fork like RGNY in Riverhead (pictured above) and Macari Vineyards in Mattituck. On the South Fork? Be sure to check out the iconic igloo experiences at either The Baker House 1650 in East Hampton, or at Gurney’s Resort in Montauk.

Other picturesque overnight stay options include Sound View in Greenport, Canoe Place Inn & Cottages in Hampton Bays, Baron’s Cove in Sag Harbor, and Aqua by American Beech in Aquebogue.


Relax and Rejuvenate at a Luxurious Spa

gurneys spa

Long Island’s diverse range of hotel spas across the region make for a great romantic getaway filled with massages, facials, bodywork treatments, and more. Escape to a spa for a Valentine’s Day rejuvenating, bliss-inducing spa weekend where heated pools and massages are sure to provide the self-care you crave. Don’t miss Gurney’s Montauk Resort & Seawater Spa, home to North America’s only ocean-fed seawater pool and indulge at Naturopathica Spa & Healing Center in East Hampton, where they connect beauty, health, community, and the earth through a holistic approach. 

Insider tip: Learn more through our Guide to Relaxation & Wellness on Long Island blog.


Classic Dinner and a Show

engeman theater

From cozy Long Island playhouses in quaint downtown villages to large performing arts centers, the Long Island theatre culture sets the stage for innovative new works and classic theater. What better way to celebrate Valentine’s Day than a classic date of a dinner and show combo. Northport Village is a quaint, thriving picture postcard, waterfront village, settled in the 1600’s – and another ideal setting for romance. Stop by for dinner at either The Northport Hotel or Arlo Kitchen and Bar in Northport, then catch a performance at the John W. Engeman Theater in the village.

Insider tip: Check out our recent LITV episode for an exclusive inside look at The Northport Hotel!

Another lovely waterfront town to explore on the north shore is Huntington. Downtown Huntington is charming with something for everyone. From shops to bars and restaurants, to theaters, and more, you can always find something to do. Make a reservation at Besito, Prime, or The Farm Italy, and then stop by The Paramount for a show.  


Chocolate, Flowers & Other Treats

disset chocolate

There’s nothing better than the gift of chocolate and flowers for your significant other this Valentine’s Day. Order a handcrafted Valentine’s Day box from Disset Chocolate with a collection that offers a medley of delicious chocolates. Olive It Boutique in Merrick also offers the perfect Valentine’s Day bundle including a mini bouquet, chocolate, and a greeting card. Want to try something different than the usual chocolate covered strawberries? Indulge in love with handcrafted cherry chocolate biscotti cookies from The Biscotti Company located in Calverton.